CN1020604C - 制备(S)-α-乙基-2-氧代-1-吡咯烷基乙酰胺的方法 - Google Patents
制备(S)-α-乙基-2-氧代-1-吡咯烷基乙酰胺的方法 Download PDFInfo
- Publication number
- CN1020604C CN1020604C CN89108764A CN89108764A CN1020604C CN 1020604 C CN1020604 C CN 1020604C CN 89108764 A CN89108764 A CN 89108764A CN 89108764 A CN89108764 A CN 89108764A CN 1020604 C CN1020604 C CN 1020604C
- Authority
- CN
- China
- Prior art keywords
- ethyl
- oxo
- alpha
- preparation
- pyrrolidineacetamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 13
- HPHUVLMMVZITSG-LURJTMIESA-N levetiracetam Chemical compound CC[C@@H](C(N)=O)N1CCCC1=O HPHUVLMMVZITSG-LURJTMIESA-N 0.000 title description 7
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 6
- 238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 3
- 235000003599 food sweetener Nutrition 0.000 claims description 4
- 239000003765 sweetening agent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- ZDGXMOZHFUQHKZ-UHFFFAOYSA-N 2-(3-ethyl-2-oxopyrrolidin-1-yl)acetamide Chemical compound CCC1CCN(CC(N)=O)C1=O ZDGXMOZHFUQHKZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- -1 (S)-alpha-ethyl-2-oxo-1-pyrrolidinyl acetamide Chemical compound 0.000 abstract description 4
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 230000000302 ischemic effect Effects 0.000 abstract description 2
- 206010001488 Aggression Diseases 0.000 abstract 1
- 206010021143 Hypoxia Diseases 0.000 abstract 1
- 230000016571 aggressive behavior Effects 0.000 abstract 1
- 208000012761 aggressive behavior Diseases 0.000 abstract 1
- 230000007954 hypoxia Effects 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 0 C[C@](C=*)N(CCC1)C1[U] Chemical compound C[C@](C=*)N(CCC1)C1[U] 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- ARUJJNVNLJPSDO-UHFFFAOYSA-N butanamide;hydrochloride Chemical compound Cl.CCCC(N)=O ARUJJNVNLJPSDO-UHFFFAOYSA-N 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229960004452 methionine Drugs 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- HNNJFUDLLWOVKZ-VKHMYHEASA-N (2s)-2-aminobutanamide Chemical compound CC[C@H](N)C(N)=O HNNJFUDLLWOVKZ-VKHMYHEASA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- 150000008319 1H-pyrimidin-2-ones Chemical class 0.000 description 1
- HNNJFUDLLWOVKZ-UHFFFAOYSA-N 2-aminobutanamide Chemical compound CCC(N)C(N)=O HNNJFUDLLWOVKZ-UHFFFAOYSA-N 0.000 description 1
- CDIIZULDSLKBKV-UHFFFAOYSA-N 4-chlorobutanoyl chloride Chemical class ClCCCC(Cl)=O CDIIZULDSLKBKV-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- PQLFROTZSIMBKR-UHFFFAOYSA-N ethenyl carbonochloridate Chemical compound ClC(=O)OC=C PQLFROTZSIMBKR-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical class CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB88.27389 | 1988-11-23 | ||
| GB888827389A GB8827389D0 (en) | 1988-11-23 | 1988-11-23 | Process for preparation of(s)alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1042904A CN1042904A (zh) | 1990-06-13 |
| CN1020604C true CN1020604C (zh) | 1993-05-12 |
Family
ID=10647345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN89108764A Expired - Fee Related CN1020604C (zh) | 1988-11-23 | 1989-11-22 | 制备(S)-α-乙基-2-氧代-1-吡咯烷基乙酰胺的方法 |
Country Status (17)
| Country | Link |
|---|---|
| KR (1) | KR0157610B1 (pt) |
| CN (1) | CN1020604C (pt) |
| AT (1) | AT392781B (pt) |
| BG (1) | BG51041A3 (pt) |
| CY (1) | CY1672A (pt) |
| ES (1) | ES2023532A6 (pt) |
| FI (1) | FI91961C (pt) |
| GB (2) | GB8827389D0 (pt) |
| GR (1) | GR1000719B (pt) |
| HK (1) | HK102492A (pt) |
| HU (1) | HU204508B (pt) |
| NO (1) | NO173823C (pt) |
| PH (1) | PH26332A (pt) |
| PL (1) | PL161781B1 (pt) |
| PT (1) | PT92365B (pt) |
| RU (1) | RU1797607C (pt) |
| SG (1) | SG89392G (pt) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9319732D0 (en) | 1993-09-24 | 1993-11-10 | Ucb Sa | Use of (s)-alpha-ethyl-2-oxo-l-pyrrolidineacetamide for the treatment of anxiety |
| US6107492A (en) * | 1998-05-08 | 2000-08-22 | Ucb, S.A. | Process for the preparation of levetiracetam |
| JP4249415B2 (ja) | 1999-12-01 | 2009-04-02 | ユセベ，ソシエテ アノニム | Ｃｎｓ疾患の治療のためのピロリジンアセトアミド誘導体単体又は組み合わせ物 |
| GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
| RU2216322C1 (ru) * | 2002-02-28 | 2003-11-20 | Закрытое акционерное общество "АСГЛ-Фармацевтические Инновации" | Средство, обладающее антиишемической, гипотензивной, противоаритмической и ноотропной активностью |
| US7132552B2 (en) * | 2003-02-03 | 2006-11-07 | Teva Pharmaceutical Industries, Ltd. | Process for producing levetiracetam |
| ES2214147B1 (es) * | 2003-02-28 | 2005-10-01 | Farma-Lepori S.A. | Procedimiento de obtencion de un agente antiepileptico. |
| JP4658937B2 (ja) * | 2003-09-24 | 2011-03-23 | ユセベ ファルマ ソシエテ アノニム | ２−オキソ−１−ピロリジン誘導体の製造方法 |
| CA2488325C (en) | 2004-11-22 | 2010-08-24 | Apotex Pharmachem Inc. | Improved process for the preparation of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide and (r)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide |
| WO2006128693A2 (en) | 2005-06-01 | 2006-12-07 | Ucb Pharma, S.A. | 2 -oxo-i -pyrrolidine derivatives/ processes for preparing them and their therapeutic use on the central nervous system |
| US8338621B2 (en) | 2005-12-21 | 2012-12-25 | Ucb S.A. | Process for the preparation of 2-oxo-1-pyrrolidine derivatives |
| WO2009050735A1 (en) * | 2007-10-15 | 2009-04-23 | Lupin Limited | A novel polymorph of levetiracetam and a process for its preparation |
| EP2147911A1 (en) | 2008-07-24 | 2010-01-27 | ZaCh System S.p.A. | Process for the preparation of levetiracetam |
| US7939676B2 (en) | 2009-09-17 | 2011-05-10 | Zach System S.P.A. | Process for the preparation of levetiracetam |
| PH12019500127B1 (en) | 2014-01-21 | 2022-05-04 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
| SMT201900545T1 (it) | 2014-01-21 | 2019-11-13 | Janssen Pharmaceutica Nv | Combinazioni comprendenti modulatori allosterici positivi o agonisti ortosterici del recettore glutammatergico metabotropico sottotipo 2 e loro utilizzo |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1309692A (en) * | 1970-02-13 | 1973-03-14 | Ucb Sa | N-substituted lactams |
| GB8412358D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
| GB8412357D0 (en) * | 1984-05-15 | 1984-06-20 | Ucb Sa | Pharmaceutical composition |
-
1988
- 1988-11-23 GB GB888827389A patent/GB8827389D0/en active Pending
-
1989
- 1989-11-20 GR GR890100769A patent/GR1000719B/el not_active IP Right Cessation
- 1989-11-20 BG BG090398A patent/BG51041A3/bg unknown
- 1989-11-21 PT PT92365A patent/PT92365B/pt not_active IP Right Cessation
- 1989-11-21 GB GB8926244A patent/GB2225322B/en not_active Expired - Lifetime
- 1989-11-22 NO NO894649A patent/NO173823C/no unknown
- 1989-11-22 AT AT2666/89A patent/AT392781B/de not_active IP Right Cessation
- 1989-11-22 ES ES8903978A patent/ES2023532A6/es not_active Expired - Lifetime
- 1989-11-22 CN CN89108764A patent/CN1020604C/zh not_active Expired - Fee Related
- 1989-11-22 FI FI895562A patent/FI91961C/fi active IP Right Grant
- 1989-11-22 HU HU896132A patent/HU204508B/hu not_active IP Right Cessation
- 1989-11-22 RU SU4742434A patent/RU1797607C/ru active
- 1989-11-22 PL PL89282413A patent/PL161781B1/pl unknown
- 1989-11-23 PH PH39568A patent/PH26332A/en unknown
- 1989-11-23 KR KR1019890017038A patent/KR0157610B1/ko not_active Expired - Fee Related
-
1992
- 1992-09-05 SG SG893/92A patent/SG89392G/en unknown
- 1992-12-17 HK HK1024/92A patent/HK102492A/xx not_active IP Right Cessation
-
1993
- 1993-05-14 CY CY1672A patent/CY1672A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI895562A0 (fi) | 1989-11-22 |
| GB8926244D0 (en) | 1990-01-10 |
| GB8827389D0 (en) | 1988-12-29 |
| HK102492A (en) | 1992-12-24 |
| PT92365B (pt) | 1995-07-18 |
| SG89392G (en) | 1992-12-04 |
| HU204508B (en) | 1992-01-28 |
| NO173823B (no) | 1993-11-01 |
| FI91961C (fi) | 1994-09-12 |
| CN1042904A (zh) | 1990-06-13 |
| PL161781B1 (en) | 1993-07-30 |
| GB2225322A (en) | 1990-05-30 |
| NO173823C (no) | 1994-02-09 |
| ATA266689A (de) | 1990-11-15 |
| AT392781B (de) | 1991-06-10 |
| NO894649D0 (no) | 1989-11-22 |
| HU896132D0 (en) | 1990-02-28 |
| GB2225322B (en) | 1992-03-25 |
| FI91961B (fi) | 1994-05-31 |
| CY1672A (en) | 1993-05-14 |
| GR890100769A (en) | 1990-12-31 |
| GR1000719B (el) | 1992-11-23 |
| PH26332A (en) | 1992-04-29 |
| NO894649L (no) | 1990-05-25 |
| BG51041A3 (bg) | 1993-01-15 |
| HUT53072A (en) | 1990-09-28 |
| KR900007797A (ko) | 1990-06-02 |
| ES2023532A6 (es) | 1992-01-16 |
| RU1797607C (ru) | 1993-02-23 |
| PT92365A (pt) | 1990-05-31 |
| KR0157610B1 (ko) | 1998-11-16 |
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